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A close-up of soft, buttery pineapple upside-down sugar cookies with a caramelized brown sugar topping, pineapple chunk, and red maraschino cherry.

Pineapple Upside Sugar Cookies

A fun twist on the classic pineapple upside-down cake, these cookies are soft, sweet, and bursting with tropical pineapple flavor. Perfect for parties or a sweet snack!
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Prep Time 20 minutes
Cook Time 12 minutes
Total Time 40 minutes
Servings: 24 cookies
Course: Dessert
Cuisine: American
Calories: 120
Ingredients Equipment Method Notes

Ingredients
  

Cookie Dough
  • 1/2 cup unsalted butter softened
  • 1 cup granulated sugar
  • 1 egg
  • 1/2 tsp vanilla extract
  • 1 1/2 cups all-purpose flour
  • 1/2 tsp baking powder
  • 1/4 tsp salt
Topping
  • 1/4 cup brown sugar
  • 24 pieces pineapple tidbits drained well
  • 12 pieces maraschino cherries halved

Equipment

  • Mixing bowls
  • Hand Mixer
  • Baking Sheet
  • Parchment Paper

Method
 

  1. Preheat oven to 350°F (175°C). Line a baking sheet with parchment paper.
  2. Cream together butter and sugar until light and fluffy. Add egg and vanilla extract, mix well.
  3. Whisk together flour, baking powder, and salt in a separate bowl. Gradually add to wet mixture and mix until combined.
  4. Scoop cookie dough onto baking sheet. Press lightly to flatten each ball.
  5. Sprinkle tops with brown sugar, then gently press a pineapple tidbit and half a cherry in the center of each cookie.
  6. Bake for 10–12 minutes until edges are lightly golden. Cool before serving.

Notes

For extra flavor, drizzle with a little pineapple glaze made from powdered sugar and pineapple juice.